Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
  • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/60—Sugars; Derivatives thereof
  • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/86—Polyethers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/54—Polymers characterized by specific structures/properties
  • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
  • A61K2800/5424—Polymers characterized by specific structures/properties characterized by the charge anionic
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/59—Mixtures
  • A61K2800/596—Mixtures of surface active compounds

Definitions

• This invention relates to mild cleaning preparations, more particularly for the washing or rinsing of hair.
• water-containing cleaning preparations normally contain surface-active compounds which generally increase the effect of the preparation on the skin. This applies in particular to the important class of anionic surfactants.
• Preparations for washing or rinsing hair for example shampoos and hair treatment preparations removable by rinsing, are of particular interest in the field of water-based cleaning preparations.
• preparations which have an improved effect in regard to the fullness and stylability of hair.
• the hair is often in a cosmetically unsatisfactory state after washing. It feels dull, is difficult to comb when wet and tends to develop static charges when dry which makes it difficult to comb and affects the set of the hair after combing.
• zwitterionic polymers containing anionic groups can be used in hair treatment preparations.
• DE-OS-21 50 557 describes the use of polymers of zwitterionic monomers in hair setting preparations.
• zwitterionic polymers are attended by the disadvantage, particularly in formulations containing anionic surfactants, that the hair-conditioning and hair-setting properties are gradually lost in the event of prolonged storage.
• DE-OS-33 26 230 describes water-containing preparations for the washing and rinsing of hair which are said to improve the fullness and stylability of the hair through the presence of special polyaldehydocarboxylic acids.
• conditioning preparations can be applied to the hair after washing or shampooing and that conditioners can be added to shampoos in order to obtain a certain conditioning effect when the hair is washed.
• conditioners include, for example, cationic polymers, for example cationic cellulose derivatives.
• European patent application EP 337 354 describes preparations containing a combination of alkyl glycosides and a cationic polymer.
• auxiliaries such as these to obtain a satisfactory improvement in wet combability and, for example with cationic surfactants, a reduction in static charging, these effects are almost always accompanied by excessive smoothing of the dry hair. This gives rise to the disadvantage that the hair lacks fullness and is unable to hold styles. The smoothness of the hair is more pronounced, the lower the combing resistance of the dry hair.
• the problem addressed by the present invention was to provide water-containing cleaning preparations, more particularly for the washing and rinsing of hair, which would combine high foaming power with a minimal effect on the skin and which would significantly reduce the smoothness of dry hair without making the hair tacky and without any adverse effect on its wet combability.
• the water-containing cleaning preparation contains from 1 to 50% by weight of an anionic surfactant, from 0.5 to 10% by weight of an alkyl glycoside and from 0.1 to 5% by weight of an anionic polymer.
• the present invention relates to water-containing cleaning preparations containing
• (A) 1 to 50% by weight of one or more anionic surfactants containing 1 or 2 lipophilic groups with 1 to 22 carbon atoms and a polar group selected from carboxylate, sulfate or sulfonate groups and optionally a polyoxyalkylene group having an average degree of alkoxylation of 1 to 15,
• a polyoxyalkylene group is understood to be a group which is made up of oxyethylene units —[CH 2 —CH—O]— or of oxypropylene units —[CH(CH 3 )—CH 2 —O]—.
• the average number of oxyethylene units or oxypropylene units is termed the average degree of alkoxylation.
• the anionic surfactants (A) are preferably selected from the group consisting of alkyl and dialkyl ether sulfates, ether carboxylic acids, sulfosuccinic acid semiesters, fatty alcohol ether citrates, fatty alcohol ether tartrates, acyl sarcosides, acyl taurides and sulfonates of unsaturated fatty acids.
• the counterions of the carboxylate, sulfate or sulfonate groups are preferably selected from the group consisting of alkali and alkaline earth metals, aluminium, ammonium and alkyl or alkylolammonium groups containing 1 to 4 carbon atoms in each alkyl or alkylol group.
• the group of alkali metals is most particularly suitable.
• Dialkyl ether sulfates are compounds of the type described in European patent application EP 299 370. Particulars of the production and properties of these compounds can be found in that document.
• Fatty alcohol ether tartrates are monoester salts of tartaric acid while fatty alcohol ether citrates are monoester and/or diester salts of citric acid with adducts of ethylene oxide and/or propylene oxide with fatty alcohols.
• Sulfonates of unsaturated fatty acids are sulfonation products of fatty acids containing 12 to 22 carbon atoms and 1 to 6 double bonds. Products such as these are known from the literature and are obtainable, for example, by reaction of these fatty acids with gaseous sulfur trioxide. Taking oleic acid as an example, particulars of their production can be found in German patent application DE 39 26 344.
• alkoxylation reactions such as, for example, the addition of x moles of ethylene oxide onto 1 mole of fatty alcohol by known methods of ethoxylation do not give an adduct per se, but rather a mixture of residues of free fatty alcohol and a series of homologous (oligomeric) addition products of 1, 2, 3, . . . x, x+1, x+2 . . . etc. molecules of ethylene oxide per molecule of fatty alcohol.
• the average degree of ethoxylation (x) is defined by the starting quantities of fatty alcohol and ethylene oxide.
• the distribution curve of the homolog mixture generally shows a maximum in the range from x ⁇ 3 to x+3. Further information on this subject can be found, for example, in the journal Soap/Cosmetics/Chemical Specialities, January 1988, page 34. However, in addition to the standard alkoxylation catalysts known from the prior art, such as sodium methanolate, catalysts leading to so-called narrow-range products may also be used (cf. for example Seifen - ⁇ umlaut over (O) ⁇ le - Fette - Wachse 1990 (116) 60).
• the percentage content of anionic surfactants is 5 to 30% by weight.
• Alkyl glycosides (B) corresponding to the general formula R—(G) x are well-known surface-active substances which can be produced from sugars and aliphatic primary C 8-22 alcohols by acetalization.
• the preferred sugar component (glycose) is glucose, although fructose, mannose, galactose, telose, gulose, allose, altrose, idose, arabinose, xylose, lyxose, libose and mixtures thereof may also be used.
• acetalization products of glucose with fatty alcohols R—OH obtainable by known methods, for example from natural fats and oils, more particularly with linear, primary, saturated and unsaturated C 8-22 fatty alcohols, are preferred by virtue of their ready availability and their favorable performance properties.
• Alkyl glycosides their production and their use as surfactants are known, for example, from U.S. Pat. No. 3,839,318, U.S. Pat. No. 3,707,535, U.S. Pat. No. 3,547,828, DE-A-1943689, DE-A-2036472, DE-A-3001064 and EP-A-77167.
• Alkyl glycosides (B), in which R is a C 8-22 alkyl group and (G), is a glycoside or oligoglycoside having a degree of oligomerization x of 1 to 4, are particularly suitable.
• R is a C 10-16 alkyl group and (G) x is the residue of a mixture of glucoside and oligoglucosides having an average degree of oligomerization of 1 to 1.5.
• the percentage content of the alkyl glycoside is 1 to 5% by weight.
• anionic polymers (C) there are no particular restrictions on the choice of the anionic polymers (C).
• polyaldehydocarboxylic acids having an average molecular weight of 600 to 10,000 and a content of 5 to 9 and preferably 7 to 9 carboxyl groups and 1 to 5 and preferably 1 to 3 aldehyde groups per 10 monomer units have proved to be particularly suitable. These products are used in the form of their water-soluble salts, more particularly their alkali metal salts.
• Polyaldehydocarboxylic acids such as these are known commercial products. They are prepared, for example, by the oxidative homopolymerization of acrolein or even by the oxidative copolymerization of acrolein and acrylic acid and are marketed, for example, by Degussa AG.
• the percentage content of the anionic polymer is 0.5 to 3% by weight.
• preparations according to the invention may contain 0.5 to 20% by weight and, more particularly, 1 to 10% by weight of ampholytic and/or zwitterionic surfactants in addition to the anionic surfactants (A).
• Ampholytic surfactants are surface-active compounds which, in addition to a C 8-18 alkyl or acyl group, contain at least one free amino group and at least one —COOH or —SO 3 H group in the molecule and are capable of forming inner salts.
• ampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkyl-aminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropyl glycines, N-alkyl taurines, N-alkyl sarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids all containing approximately 8 to 18 carbon atoms in the alkyl group.
• Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one —COO ( ⁇ ) or —SO 3 ( ⁇ ) group in the molecule.
• Particularly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl-N,N-dimethyl-ammonium glycinates, for example coconut oil alkyl dimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinate, for example coconut oil acylaminopropyl dimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines containing 8 to 18 carbon atoms in the alkyl or acyl group and also coconut oil acylaminoethyl hydroxyethyl carboxymethyl glycinate.
• preparations according to the invention on the skin is particularly pronounced when the preparations are formulated in such a way that they have a pH value in the vicinity of the neutral point of the skin. Accordingly, preparations having pH values in the range from 4.0 to 7.5 and, more particularly, in the range from 4.5 to 7.0 are preferred.
• the preparations according to the invention may contain inorganic electrolyte salts (E).
• Suitable inorganic electrolyte salts are any water-soluble alkali metal, ammonium and alkaline earth metal salts, for example the fluorides, chlorides, bromides, sulfates, phosphates and nitrates and hydrogen carbonates, providing they are soluble in water in a quantity of at least 1% by weight at 20° C.
• the chlorides or sulfates of an alkali metal, ammonium or magnesium are preferably used, sodium chloride and magnesium chloride being particularly preferred.
• the electrolyte salt is preferably present in a quantity of 0.1 to 10% by weight.
• the preparations according to the invention may be used in a number of commercial cleaning products, such as hair shampoos, foam baths, shower baths, liquid soaps and manual dishwashing detergents. They are particularly suitable for mild hair shampoos which leave the hair with improved fullness and stylability.
• the products in question typically contain such constituents as emulsifiers, oil components, solubilizers, thickeners, superfatting agents, biogenic agents, film formers, fragrances, dyes, pearlescers, foam stabilizers, preservatives and pH regulators. Accordingly, the preparations according to the invention may contain additional components and auxiliaries as known from the prior art. The most important are:
• Surfactants/emulsifiers for example anionic surfactants containing carboxylate, sulfonate, sulfate or phosphate groups, such as soaps, alkyl and aryl ether sulfates, fatty amines, quaternary ammonium and pyridinium compounds, nonionic emulsifiers, such as ethylene oxide adducts with alcohols, carboxylic acids, partial glycerides and sorbitan esters, amphoteric and zwitterionic emulsifiers, such as imidazoline derivatives, betaines or sulfobetaines and, for example, fatty acid esters and sorbitan fatty acid esters (cf. for example W. Umbach [Ed.] “ Kosmetik -technisch, Kunststoff für kosmetischer Mittel”, pages 86-87, Stuttgart 1988).
• Oil components for example substances such as paraffin oil, vegetable oils, fatty acid esters, squalane and 2-octyl dodecanol; as fats and waxes, for example spermaceti, beeswax, montan wax, paraffin and cetostearyl alcohol.
• Solubilizers for example lower monohydric or polyhydric alcohols, such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol, 1,3-butylene glycol and diethylene glycol.
• lower monohydric or polyhydric alcohols such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol, 1,3-butylene glycol and diethylene glycol.
• Thickeners for example polysaccharides, more particularly xanthan gum, guar gum, agar agar, alginates and tyloses; carboxymethyl cellulose and hydroxyethyl cellulose; relatively high molecular weight polyethylene glycol monoesters and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolidone.
• Superfatting agents for example polyethoxylated lanolin derivatives, lecithin derivatives and fatty acid alkanolamides, the latter also acting as foam stabilizers.
• Biogenic agents such as plant extracts, protein degradation products and vitamin complexes.
• Film formers such as polyvinyl pyrrolidone, vinyl pyrrolidone/vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives and similar compounds.
• Humectants for example glycerol, polyglycerols, sorbitol, propane-1,2-diol, butane-1,2,3-triol, polyethylene glycols, glucose, mannitol, xylitol, pyrrolidone carboxylic salts (PCA), amino acids, lactic acid.
• PCA pyrrolidone carboxylic salts
• Antimicrobial agents as preservatives for example benzoic acid, salicylic acid, sorbic acid, esters and salts thereof and the substances listed in the “ 7-9 Kosmetikver extract ( Appendix to the Cosmetics Act )”.
• Pearlescers such as glycol distearic acid esters, ethylene glycol distearate or fatty acid monoglycol esters.
• Fragrances for example natural fragrances obtained from plants by distillation, extraction or pressing and synthetic fragrances (cf. for example H. Aebi, E. Baumgartner, H. P. Fiedler, G. Ohloff, “ Kosmetika, Riechstoffe und Anlagenberichtstoffe ”, Stuttgart 1978).
• Antioxidants for example tocopherols, lecithin, guaiacol, butyl cresol, 4-methyl-2,6-ditert.butylphenol (BHT), 4-methoxy-2(3)tert.butylphenol (BHA).
• BHT 4-methyl-2,6-ditert.butylphenol
• BHA 4-methoxy-2(3)tert.butylphenol
• pH regulators other components of the preparations according to the invention are, if desired, substances of which the function is to adjust the pH value of the preparations.
• the auxiliaries are present in total quantities of 0 to 20% by weight and preferably 0 to 10% by weight.
• the alkyl glycoside (B) is added at 60 to 80° C. to an aqueous phase containing the anionic surfactants (A), the anionic polymer (C) and the electrolyte salt (D). These mixtures are stirred and then cooled to normal temperature (20 to 40° C.).
• the preparations according to the invention may also be produced with advantage in the absence of heat. In this case, the components are merely stirred together at normal temperature.
• N25 Aqueous solution of sodium lauryl ether sulfate; active substance content: 28% by weight (“Texapon® N25”; a product of Henkel KGaA, D ⁇ umlaut over (u) ⁇ sseldorf) 1,
• Dehyton K Aqueous solution of a fatty acid amide derivative of betaine structure with the formula R—CONH—(CH 2 ) 3 —N + (CH 3 ) 2 —CH 2 —COO ⁇ ;
• CTFA name Cocamidopropyl Betaine; active substance content: 30% by weight; NaCl content: 5% by weight (a product of Henkel KGaA, D ⁇ umlaut over (u) ⁇ sseldorf)
• AKYP Aqueous solution of an ether carboxylic acid salt with the formula C 12/14 —(O—CH 2 —CH 2 ) 10 —OCH 2 —COONa, active substance content: 22% by weight (“Akypo®-Soft 100 NV”; a product of Chemy-Y)
• APG600 C 12/14 fatty alcohol glucoside with a degree of oligomerization of 1.45 (a product of Henkel KGaA, D ⁇ umlaut over (u) ⁇ sseldorf).
• Nutrilan I Protein hydrolyzate
• CTFA name Hydrolyzed Animal Collagen (“Nutrilan® I”; a product of Gr ⁇ umlaut over (u) ⁇ nau, Illertissen)
• POC Aqueous solution of poly(aldehydocarboxylic acid) sodium salt; active substance content: 40% by weight; average molecular weight: 5,000 (“POC-HS-5060”; a product of Degussa AG)
• Dry combability was tested on brown hair (Alkinco #6634, tress length 12 cm, tress weight 1 g). The hair used was slightly predamaged (bleached) hair as might be expected of the average user. After the zero measurement, the tresses were soaked with 100 ml of the formulation to be tested. After a contact time of 5 minutes, the tresses were rinsed for 1 minute in running water (1 l/min., 38° C.). The tresses were then dried for 12 hours at 30° C./20% relative air humidity and thereafter were remeasured and the results were compared with the zero measurement. The results of the dry combability tests are set out in Table 1.
• Example E1 according to the invention shows distinctly higher dry combability than C1 and C2. Since DC is a measure of style holdability, E1 shows an improvement in style holdability.
• Example E2 according to the invention shows a distinctly lower wet combability value by comparison with C3 and C4. Since lower WC values signify a better combability of wet hair, E2 shows an improvement in wet combability.
• a hair tress was suspended in a double Faraday cage. There was no conductive connection between the inner and outer cages. The outer cage was connected to a zero potential (ground). A voltmeter measured potential differences between the inner and outer cages. Potential differences always arise when, under the effect of friction during combing, charges are displaced from the surfaces of the hair fibers and collect on the surface of the comb. The electrical field and the tresses oppositely charged by comparison with the comb interact with the inner Faraday cage. The inner Faraday cage develops an opposite charge on the inside (influence). The charge displacement relative to the outer cage was recorded on the voltmeter and was a direct measure of the triboelectric charging of the combed hair tresses.
• Example E3 according to the invention shows a considerably lower electrostatic charging value by comparison with C5 and C6.
• Lower EC values signify a reduced tendency of the hair fibers to repel and to “fly away” from one another.
• the foam was produced at room temperature using a perforated plate (bores 1 mm in diameter, 10 beats at a frequency of 50 beats per minute, 13 cm stroke). The foam was very fine and thus largely corresponded to the foam formed on the hair during shampooing. The measurements were carried out as double determinations with no fats in the surfactant solution.
• Example E4 according to the invention shows a distinctly larger quantity of foam by comparison with C7 and C8.
• the skin compatibility of the cleaning preparations was determined by the in vitro method developed by Zeidler and Reese which is described in detail in the journal ⁇ umlaut over (A) ⁇ rête Kosmetologie 13, 39-45 (1983).
• the swelling of porcine epidermis was used as a measure of the skin compatibility of the cleaning preparations.
• the epidermis required was taken from freshly slaughtered young pigs and deep frozen.
• epidermis strips measuring 1 cm ⁇ 6 cm were cut out and immersed for 30 minutes in a solution which had been prepared by diluting the water-containing cleaning preparation with water in such a way that it contained 2% by weight active substance of surfactants.
• the solution was kept at 39° C. and adjusted to pH 6.5.
• the weight of the swollen strips was determined.
• the strips were then dried over calcium chloride for 24 hours and reweighed. In order to eliminate influences attributable to specific properties of the particular animal and the point of removal (back, flank), a standard measurement was carried out in each case. To this end, an immediately adjacent epidermis strip is similarly treated with water instead of the water-containing cleaning preparation.
• the Q value of the water-treated skin is 0%.
• Negative values indicate swelling-inhibiting properties.
• Example E5 according to the invention shows improved swelling values by comparison with C9 and C10.

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• Life Sciences & Earth Sciences (AREA)
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• Birds (AREA)
• Epidemiology (AREA)
• Cosmetics (AREA)
• Detergent Compositions (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

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• 1991
  • 1991-09-02 DE DE4129124A patent/DE4129124A1/de not_active Withdrawn
• 1992
  • 1992-08-24 CA CA002116846A patent/CA2116846C/fr not_active Expired - Fee Related
  • 1992-08-24 ES ES92917679T patent/ES2083759T3/es not_active Expired - Lifetime
  • 1992-08-24 DE DE59205318T patent/DE59205318D1/de not_active Expired - Lifetime
  • 1992-08-24 EP EP92917679A patent/EP0602078B1/fr not_active Expired - Lifetime
  • 1992-08-24 US US08/204,150 patent/US6172018B1/en not_active Expired - Lifetime
  • 1992-08-24 WO PCT/EP1992/001940 patent/WO1993004662A1/fr not_active Ceased
  • 1992-08-24 DK DK92917679.0T patent/DK0602078T3/da active
  • 1992-08-24 JP JP50489493A patent/JP3608787B2/ja not_active Expired - Lifetime
  • 1992-08-24 AT AT92917679T patent/ATE133852T1/de not_active IP Right Cessation
  • 1992-09-01 MX MX9205020A patent/MX9205020A/es unknown
• 1996
  • 1996-04-02 GR GR960400918T patent/GR3019528T3/el unknown

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